39201-82-6

Basic information

• Product Name: 4-Ethoxy-3,5-dimethoxybenzeneethanamine
• Synonyms: 3,5-Dimethoxy-4-ethoxyphenethylamine;4-Ethoxy-3,5-dimethoxybenzeneethanamine;Escaline;2-(4-ethoxy-3,5-diMethoxyphenyl)ethanaMine
• CAS NO: 39201-82-6
• Molecular Formula: C₁₂H₁₉NO₃
• Molecular Weight: 225.28
• Mol File: 39201-82-6.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 327.591 °C at 760 mmHg
• Flash Point: 153.439 °C
• Appearance: /
• Density: 1.051 g/cm³
• Vapor Pressure: 0.0002mmHg at 25°C
• Refractive Index: 1.508
• PKA: 9.58±0.10(Predicted)
• CAS DataBase Reference: 4-Ethoxy-3,5-dimethoxybenzeneethanamine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Ethoxy-3,5-dimethoxybenzeneethanamine(39201-82-6)
• EPA Substance Registry System: 4-Ethoxy-3,5-dimethoxybenzeneethanamine(39201-82-6)

Safety Data

• Hazardous Substances Data: 39201-82-6(Hazardous Substances Data)

Usage

Description

4-Ethoxy-3,5-dimethoxybenzeneethanamine, also known as Escaline, is a derivative of Phenethylamine (P321335), a psychoactive drug and stimulant that influences dopamine levels. It functions as a neuromodulator or neurotransmitter in the mammalian central nervous system, making it a significant compound for various applications.

Uses

Used in Pharmaceutical Industry:
4-Ethoxy-3,5-dimethoxybenzeneethanamine is used as a psychoactive agent for its ability to affect dopamine levels in the central nervous system. Its neuromodulatory and neurotransmitter properties make it a potential candidate for the development of treatments for various neurological and psychiatric disorders.
Used in Research and Development:
In the field of research and development, 4-Ethoxy-3,5-dimethoxybenzeneethanamine is used as a chemical compound for studying the effects of Phenethylamine derivatives on the central nervous system. This can contribute to the understanding of neuromodulation and neurotransmission, potentially leading to the discovery of new therapeutic approaches for related conditions.
Used in Drug Delivery Systems:
Similar to Gallotannin, 4-Ethoxy-3,5-dimethoxybenzeneethanamine could be employed in drug delivery systems to enhance its applications and efficacy. By utilizing various organic and metallic nanoparticles as carriers, its delivery, bioavailability, and therapeutic outcomes could be improved, making it a more effective compound for targeted treatments.
Please note that the provided materials do not specify any particular application for 4-Ethoxy-3,5-dimethoxybenzeneethanamine, so the uses listed above are inferred based on its classification as a Phenethylamine derivative and its potential roles as a neuromodulator or neurotransmitter.

InChI:InChI=1/C12H19NO3/c1-4-16-12-10(14-2)7-9(5-6-13)8-11(12)15-3/h7-8H,4-6,13H2,1-3H3

Synthetic route

3,5-Dimethoxy-4-ethoxy-ω-nitrostyrol (54110-92-8) → Escaline (39201-82-6)

Conditions	Yield
With lithium aluminium tetrahydride; diethyl ether

(4-Ethoxy-3,5-dimethoxy-phenyl)-acetonitrile (61367-64-4) → Escaline (39201-82-6)

Conditions	Yield
With hydrogenchloride; hydrogen; palladium on activated charcoal In ethanol
With hydrogenchloride; palladium; acetic acid Hydrogenation;

4-hydroxy-3,5-dimethoxyphenylacetonitrile (42973-55-7) → Escaline (39201-82-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: K2CO3 / acetone 2: H2, aq. HCl / Pd-C / ethanol View Scheme

Upstream product

• 54110-92-8 3,5-Dimethoxy-4-ethoxy-ω-nitrostyrol 
• 42973-55-7 4-hydroxy-3,5-dimethoxyphenylacetonitrile 
• 61367-64-4 (4-Ethoxy-3,5-dimethoxy-phenyl)-acetonitrile 

Relevant articles and documents

Lipophilicity and serotonin agonist activity in a series of 4 substituted mescaline analogues

Replacement of the 4 methoxy of mescaline with higher alkyl homologues or with bromine led to increased activity at serotonin receptors in a sheep umbilical artery preparation. This activity appears correlated with lipophilicity, as measured by 1 octanol water partition coefficients, but drops off when the 4 substituent is about five atoms in length. It is suggested that 3,4,5 trisubstitution may give compounds which are as active as those with the 2,4 5 substitution pattern.